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Sanders's first marriage unfolded in 1989 to Caroline Chambers, a union that produced two children: Deandra Sanders and Dion Jr. Their courtship, which began rather humorously when Chambers recalled Sanders introducing himself with his "Prime Time" moniker, sadly culminated in divorce in 1998. This separation didn't shackle Sanders; he soon ventured into another marriage with Pilar Biggers in 1999, a relationship that saw the birth of three more children. Out of genuine love and extravagant gestures, Sanders and Pilar's bond appeared unwavering for years. However, their marriage unraveled amid a contentious divorce filled with trials, leading to their finalized separation in 2013.